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PSB-SB-487

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This is an old revision of this page, as edited by DePiep (talk | contribs) at 20:23, 2 April 2016 (Remove redundant parameters InChI, InChIKey (StdInChI, StdInChIKey are used). See Talk (via AWB script)). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

PSB-SB-487
Identifiers
  • 7-(1,1-Dimethyloctyl)-5-hydroxy-3-(2-hydroxybenzyl)-2H-chromen-2-one
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H32O4
Molar mass408.53 g·mol−1
3D model (JSmol)
  • OC1=C(CC2=CC3=C(C=C(C(C)(C)CCCCCCC)C=C3O)OC2=O)C=CC=C1
  • InChI=1S/C26H32O4/c1-4-5-6-7-10-13-26(2,3)20-16-23(28)21-15-19(25(29)30-24(21)17-20)14-18-11-8-9-12-22(18)27/h8-9,11-12,15-17,27-28H,4-7,10,13-14H2,1-3H3
  • Key:YNWOMOUVWNKICO-UHFFFAOYSA-N

PSB-SB-487 is a coumarin derivative which is an antagonist at the former orphan receptor GPR55. Unlike older GPR55 antagonists such as O-1918, PSB-SB-487 has good selectivity over the related receptor GPR18, with an IC50 of 113nM at GPR55 vs 12500nM at GPR18.[1] However it has poorer selectivity over other related receptors, acting as a weak antagonist at CB1 with a Ki of 1170nM, and a partial agonist at CB2 with a Ki of 292nM.[2]

See also

References

  1. ^ Rempel, V.; Volz, N.; Gläser, F.; Nieger, M.; Bräse, S.; Müller, C. E. (2013). "Antagonists for the orphan G protein-coupled receptor GPR55 based on a coumarin scaffold". Journal of Medicinal Chemistry. 56 (11): 130516144836005. doi:10.1021/jm4005175. PMID 23679955.
  2. ^ Rempel V, Volz N, Hinz S, Karcz T, Meliciani I, Nieger M, Wenzel W, Bräse S, Müller CE. 7-Alkyl-3-benzylcoumarins: a versatile scaffold for the development of potent and selective cannabinoid receptor agonists and antagonists. Journal of Medicinal Chemistry. 2012 Sep 27;55(18):7967-77. PMID 22916707


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